XV. Researches on acids of the lactic series.—No. 1. Synthesis of acids of the lactic series
With the exception of the acetic series, no family of organic acids has excited so much interest amongst chemists, and been the subject of such numerous researches, as that represented by lactic acid. Its character, intermediate between the monobasic and dibasic acids, its close relations to the acetic and acrylic families, and the numerous important transformations which it undergoes, have all contributed to render this family an attractive subject for experimental inquiry and a fruitful source of theoretical speculation. These inquiries and hypotheses have contributed greatly to the elucidation of the habits of these acids, and still more to the general progress of organic chemistry. Nevertheless there are two circumstances which have materially interfered with their complete success; these are, the comparatively small number of the known members of this series, and the absence of any synthetical proof of the nature of their constituent radicals. These obstacles to a more satisfactory conception of the internal architecture of the acids in question we have endeavoured to remove by the production, according to purely synthetical methods, of a number of new members of this series, a brief notice of which we have from time to time had the honour of submitting to the Royal Society, and the more complete history of which we propose to develope in the following pages. Our general method for synthetically producing the acids of the lactic series depends upon the replacement of one of the atoms of dyad oxygen in oxalic acid, or rather in the ethereal salts of oxalic acid, by two atoms of monad alcohol radicals. Such a replacement at once transforms dibasic oxalic acid into a monobasic acid of the lactic series. The nature of this transformation, as well as the relations of oxalic acid to the lactic family, is clearly seen from the following comparison of the formulae of oxalic acid and of its derivative, dimethoxalic acid.